Jake is the quarterback on the football team of the school that Dean attends. He is handsome, popular, and gets along well with almost everyone. However, once in the Greenway, he becomes very unstable after becoming completely sterile. He begins to drink and use heavy drugs, relying on these things due to his feelings of worthlessness. He is the first to leave the group after being sent out to see if the hospital was still open and then abandoning the rest of the 14. His later whereabouts can be found in Jake and the Other Girl.

In Sky On Fire, he returned to the store, only to witness Astrid and Dean having wild sex. Astrid then said that this was the bloodlust of the type O's controlling them. She then announced she was pregnant and Jake was delighted. Jake then helped Dean out of being killed by the Air Force Cadets, who captured the school bus while Niko and the rest were taking it to Denver. Jake was then saved by Captain McKinley.

In Savage Drift, Jake left with Dean, Niko and Astrid to find Josie in Missouri. They then hitched a ride with a trucker, who was then shot by a person who paranoid from a drift. They then came across the woman with a van, who was then murdered by a type O.

Eventually, Jake chooses to leave the group and go to Texas in hopes of finding his mother. During the final chapter of Savage Drift, it was noted that Astrid and Dean wanted Jake to be apart of his child's life but it is unknown if he agreed to it.

Characters in Monument 14
Monument 14: Alex Grieder · Astrid Heyman · Batiste · Brayden Cutlass · Caroline McKinley · Chloe · Dean Grieder · Henry McKinley · Jake Simonsen · Josie Miller · Max · Niko Mills · Sahalia · Ulysses
Other: Cory Booker · Mr. Reed · Trish Greenstein · Mrs. Wooly